Hydrochloric Acid → HCID 86608810, compound

HRID 1987767Notes

Reaction equation

HRID 1987767 reaction equation
[N+:1]([C:4]1[CH:27]([CH3:28])[CH:8]2[CH2:9][C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[NH:24][N:23]=[CH:22][CH:21]=4)=[C:16]([NH:25][CH3:26])[CH:15]=3)([CH3:12])[O:11][C:7]2=[C:6]([CH3:29])[C:5]=1[CH3:30])([O-])=O.C(O)C.Cl.[OH-].[Na+]>O>[NH2:1][C:4]1[CH:27]([CH3:28])[CH:8]2[CH2:9][C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[NH:24][N:23]=[CH:22][CH:21]=4)=[C:16]([NH:25][CH3:26])[CH:15]=3)([CH3:12])[O:11][C:7]2=[C:6]([CH3:29])[C:5]=1[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86608811HCID 86608811, compound

Product 1

HCID 86608810HCID 86608810, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.26 g of 5-(4-(±)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)methylaminophenyl) pyrazole, 10 ml of ethanol was added and 0.43 g of stannous chloride dihydrate and 3 ml of concentrated hydrochloric acid were added, followed by heating at reflux for 2 hours. The reaction solution was poured into water, neutralized with a sodium hydroxide solution and then extracted with chloroform. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 0.22 g of the objective product (melting point: 113-117° C.)

Workup

  1. temperatureby heating
  2. temperatureat reflux for 2 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-f790523897ec4e1b86221a29ae96330a
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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